Abstract
A series of 12 substituted (Z)-4-phenyl-3-buten-l-ol (PBO) derivatives were synthesized and evaluated for trail-following activity in five species of subterranean termites in the generaCoptotermes, Prorhinotermes, Reticulitermes, andSchedorhinotermes (Isoptera: Rhinotermitidae). The unsubstituted parent PBO was the most active for all species, and electron-withdrawing and electron-donating groups both reduced potency. Sensitivity to substitution in the ortho position suggests steric inhibition of binding by the 2′-substituted analogs. Different sensitivities to these pheromone analogs were found among the five species, withR.flavipes andS. lamanianus showing the highest level of trail-following activity for the PBO analogs.
Similar content being viewed by others
References
Akkerboom, P.J. 1974 Dodecatrienolen als spoorvolgferomonen: synthese en biologische activiteit. Thesis. Universiteit Utrecht, 54 pp.
Carvalho, J.F., andPrestwich, G.D. 1984 Synthesis of ω-tritiated and ω-fluorinated analogues of the trail pheromone of subterranean termites.J. Org. Chem. 49:1251–1258.
Hansch, C., andLeo, A. 1979 Substituent Constants for Correlation Analysis in Chemistry and Biology. Wiley-Interscience, New York.
Howard, R., Matsumura, F., andCoppel, H.C. 1976Trail-following pheromones of the Rhinotermitidae: Approaches to their authentication and specificity.J. Chem. Ecol. 2:147–166.
Howard, R.W., McDaniel, C.A., Nelson, D.R., Blomquist, G.J., Gelbaum, L.T., andZalkow, L.H. 1982 Cuticular hydrocarbons ofReticulitermes virginicus and their role as potential species- and caste-recognition cues.J. Chem. Ecol. 8:1227–1235.
Kaib, M., Bruinsma, O., andLeuthold, R.H. 1982 Trail-following in termites: Evidence for a multicomponent system.J. Chem. Ecol. 8:1193–1205.
Kajiwara, T., Sekiya, J., andHatanaka, A. 1978 Synthetic analogues of the termite trail-following substance.Agric. Biol. Chem. 42:1293–1294.
Kofron, W.G., andBaclawski, L.M. 1976 A convenient method for estimation of alkyllithium concentration.J. Org. Chem. 41:1879–1880.
Matsumura, F., Jewett, D.M., andCoppel, H.C. 1972 Interspecific response of termites to synthetic trail-following substances.J. Econ. Entomol. 65:600–602.
Matsumura, F., Nishimoto, K., Ideda, T., andCoppel, H.C. 1976. Influence of carbon sources in the trail-following substance byGleophyllum trabeum.J. Chem. Ecol. 2:299–305.
Metcalf, R.L., Mitchell, W.C., andMetcalf, E.R. 1983. Olfactory receptors in the melon flyDacus curcurbitae and the oriental fruit flyDacus dorsalis.Proc. Nat'l. Acad. Sci. (U.S.A.) 80:3143–3147.
Negishi, E., King, A.O., Klima, W.L., Patterson, W., andSilveira, A. 1980 Conversion of methyl ketones into terminal acetylenes and (E)-trisubstituted olefins of terpenoid origin.J. Org. Chem. 45:2526–2528.
Oloo, G.W., andMcDowell, P.G. 1982 Interspecific trail-following and evidence of similarity of trails ofTrinervitermes species from different habitals.Insect Sci. Appl. 3:157–161.
Pignatello, J.J., andGrant, A.J. 1983 Structure-activity correlations among analogs of 4-methyl-3-heptanol, a pheromone component of the European bark beetle (Scolytus multistriatus).J. Chem. Ecol 9:615–643.
Prestwich, G.D. 1983 Chemical systematics of termite exocrine secretions.Annu. Rev. Ecol. System. 14:287–301.
Prestwich, G.D., Mauldin, J.K., Engstrom, J.B., Carvalho, J.F., andCupo, D.Y. 1983 Comparative toxicity of fluorinated lipids and their evaluation as bait-block toxicants for the control ofReticulitermes spp. (Isoptera: Rhinotermitidae)J. Econ. Entomol. 76:690–695.
Prestwich, G.D., Melcer, M.E., andPlavcan, K.A. 1981 Fluorolipids as targeted termicides and biochemical probes.J. Agric. Food Chem. 29:1023–1027.
Ritter, F.J., Bruggeman, I.E.M., Persoons, C.J., Talman, E., van Oosten, A.M., andVerwiel, P.E.J. 1977 Evaluation of social insect pheromones in pest control, with special reference to subterranean termites and pharaoh's ants, pp. 201–216,in N. R. McFarlane (ed.),Crop Protection Agents: Their Biological Evaluation. Academic Press, New York.
Ritter, F.J., andPersoons, C.J. 1975 Recent development in insect pheromone research, in particular in the Netherlands.Neth. J. Zool. 3:261–275.
Sokal, R.R., andRohlf, F.J. 1981 Biometry, 2nd ed. W.H. Freeman, San Francisco.
Tai, A., Matsumura, F., andCoppel, H.C. 1969 Chemical identification of the trail-following pheromone for a Southern subterranean termite.J. Org. Chem. 34:2180–2182.
Tai, A., Matsumura, F., andCoppel, H.C. 1971 Synthetic analogues of the termite trail-following pheromone: Structure and biological activity.J. Insect Physiol. 17:181–188.
Author information
Authors and Affiliations
Additional information
Fellow of the Alfred P. Sloan Foundation (1981–85) and Camille and Henry Dreyfus Teacher-Scholar (1981–86).
Rights and permissions
About this article
Cite this article
Prestwich, G.D., Eng, W.S., Deaton, E. et al. Structure-activity relationships among aromatic analogs of trail-following pheromone of subterranean termites. J Chem Ecol 10, 1201–1217 (1984). https://doi.org/10.1007/BF00988549
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00988549